How a Serial Entrepreneur From Colorado Uses Her HSA

How does a serial entrepreneur from Colorado use her HSA? We chatted with Jessi Burg and explored how she leverages her HSA to help her retire early.

How a Serial Entrepreneur From Colorado Uses Her HSA

Name: Jessi Burg

Pronouns: She/Her

Occupation: Self-Employed

Industry: Landscaping

Age: 36

HSA Type (Individual, Family): Family, through spouse's work


Tell us about yourself.

I am a serial entrepreneur focused on creating sustainable companies in the trades and services. Right now, I’m launching Outgrow your Garage, which is an online learning platform about how to grow your solo business into its first few employees. In my free time, I spend a lot of time traveling, eating locally sourced food, and spending as much time outside as possible. One of my big life goals is to be able to travel on a full time basis, and spend a month or two in a location with my spouse and our dog before moving on to a new place. 

What made you choose an HDHP?

Currently, we’re young and healthy, and our health care expenses are fairly low. We like the idea of being able to save for an emergency or a long term goal, like potential long term care or lasik. 


Do you ever spend out of your HSA or are you religious about saving it all?

We tend to spend it in big chunks. For example, this year, my spouse wanted to close an old account, so we took a bunch of old receipts, cashed out the account, and then added that money to our brokerage accounts. But the money never hits our regular spending categories, it just gets moved into a different savings account. 

We’re pretty religious about scanning in all of our receipts so when we do want to move money around, we have a backlog of healthcare expenses to submit.

Any unexpected items that you found were HSA eligible? 

My therapy was covered, so that’s been super helpful for my mental health. 

Do you always max your HSA out? 

Absolutely. It’s one of the best ways for saving for emergencies that we have.


How do you balance your HSA with your other retirement accounts? 

We max everything out, but are talking about prioritizing our HSA more as we cut back retirement savings in other ways. We’re hoping to have enough saved to semi-retire well before 59 ½, so we’re starting to save more in other ways as our retirement accounts grow. 

Do you have any fun hacks or tips for folks just getting started with an HSA?

Honestly, put whatever you can into it, and think of it like a savings account. A lot of people think of it like a reimbursement account, but I’ve found that if I’m able to pay for my healthcare expenses up front, I don’t need the reimbursement as much because the money is already spent. This was extremely helpful a few years ago when I was injured and ended up with a bad infection. Even with insurance, we ended up with several thousand dollars in medical bills. Having the backlog of HSA funds made it much easier to absorb those costs and allowed us to choose a more aggressive method of treatment to get things under control.

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